This invention relates to novel N-alkyl derivatives of deoxygalactonojirimycin (DGJ) in which said alkyl groups contain from 3-6 carbon atoms. These novel compounds are useful for selectively inhibiting glycolipid synthesis.
In applicants' copending application Ser. No. 08/061,645, filed May 13, 1993, now U.S. Pat. No. 5,399,567 certain N-alkyl derivatives of deoxynojirimycin (DNJ) are disclosed as effective inhibitors of glycolipid biosynthesis. N-alkylated derivatives of DNJ were also previously known to be inhibitors of the N-linked oligosaccharide processing enzymes, .alpha.-glucosidase I and II. Saunier et al., J. Biol. Chem. 257, 14155-14166 (1982); Elbein, Ann. Rev. Biochem. 56, 497-534 (1987). As glucose analogues, they also have potential to inhibit glucosyltransferases. Newbrun et al., Arch. Oral Biol. 28, 516-536 (1983); Wang et al., Tetrahedron Lett. 34, 403-406 (1993). Their inhibitory activity against the glucosidases has led to the development of these compounds as antihyperglycemic agents and antiviral agents. See, e.g., PCT Int'l. Appln. WO 87/03903 and U.S. Pat. Nos.: 4,065,562; 4,182,767; 4,533,668; 4,639,436; 4,849,430; 5,011,829; and 5,030,638.